Triphenylphosphine → (2-(Benzyloxy)-3,5-difluorophenethyl)triphenylphosphonium, iodide salt

HRID 921171Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][I:17])=[CH:13][C:12]([F:18])=[CH:11][C:10]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]1[CH:25]=[CH:24][C:23]([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[I-:17].[CH2:1]([O:8][C:9]1[C:10]([F:19])=[CH:11][C:12]([F:18])=[CH:13][C:14]=1[CH2:15][CH2:16][P+:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:23]1[CH:22]=[CH:21][CH:20]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(benzyloxy)-1,5-difluoro-3-(2-iodoethyl)benzene (630 mg, 1.684 mmol) in toluene (8 ml) was added Ph3P (442 mg, 1.684 mmol) and the mixture was heated at 100° C. for 16 h. The mixture was then cooled to rt and toluene was decanted via pipet and remaining residue was washed with ether and ethyl acetate, dried under high vac to afford (2-(benzyloxy)-3,5-difluorophenethyl)triphenylphosphonium, iodide salt (600 mg, 0.943 mmol, 56.0% yield) as white solid. Used as-is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.81-7.71 (m, 9H), 7.62 (td, J=7.8, 3.5 Hz, 5H), 7.39-7.33 (m, 2H), 7.31 (d, J=7.6 Hz, 1H), 7.25 (d, J=7.3 Hz, 2H), 7.22-7.14 (m, 2H), 6.75 (ddd, J=11.2, 8.2, 2.8 Hz, 1H), 5.01 (s, 2H), 3.92 (dt, J=12.4, 7.9 Hz, 2H), 3.02-2.94 (m, 2H).

Workup

temperatureThe mixture was then cooled to rt
customtoluene was decanted via pipet
washwas washed with ether and ethyl acetate
customdried under high vac

Sources & evidence

ORD record: ord-422f9a97f98349b5b0be0c29295f6d0e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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